Studies toward the synthesis of popolohuanone E: Synthesis of natural (+)-arenarol related to the proposed biogenetic precursor of popolohuanone E

Tetrahedron Letters

Volumn 38, Issue 44, 1997, Pages 7769-7772

  Kawano, Hideki ^a   Itoh, Masanori ^a   Katoh, Tadashi ^a   Terashima, Shiro ^a  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARENAROL; ENZYME INHIBITOR; KETONE DERIVATIVE; POPOLOHUANONE E; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENZYME INHIBITION; HYDROGENATION;

EID: 0030665460     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10075-2     Document Type: Article

References (22)

1. Visiting scientist from Research Laboratories, Research and Development Division, Sumitomo Pharmaceutical Co. Ltd.
2. Carney, J. R., Scheuer, P. J., Tetrahedron Lett., 1993, 34, 3727-3730.
3. 6'-Hydroxyarenarol (3) has not been isolated to date because this putative compound seems to be unusually unstable and/or prone to oxidation. 2
4. Ueki, Y., Itoh, M., Katoh, T., Terashima, S., Tetrahedron Lett., 1996, 37, 5719-5722.
5. Schmitz, F. J., Lakshmi, V., Powell, D. R., van der Helm, D., J. Org. Chem., 1984, 49, 241-244.
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7. Urban, S., Capon, R. J., Aust. J. Chem., 1994, 47, 1023-1029.
8. Watson, A. T., Park, K., Wiemer, D. F., J. Org. Chem., 1995, 60, 5102-5106.
9. Hagiwara, H., Uda, H., J. Org, Chem., 1988, 53, 2308-2311.
10. The ee was determined by HPLC analysis using chiralcel OD-H column (Daicel Chemical Industries, LTD.).
11. The stereocontrolled hydrogenation of 10 was carried out according to the reported procedure with several improvements in the reaction conditions. See, Park, K., Scott, W. J., Wiemer, D. F., J. Org. Chem., 1994, 59, 6313-6317.
12. Details of X-ray crystallographic study will be reported in a separate paper.
13. For recent reviews on the Claisen rearrangement, see, a) Wipf, P., in Comprehensive Organic Synthesis, Trost, B. M., Ed., Pergamon Press, Oxford, 1991, Vol. 5, pp 827-873.
14. b) Ziegler, F. E., Chem. Rev., 1988, 88, 1423-1452.
15. 3 hybridization at the C-5 dioxolane. Detailed discussion on this issue will be presented in a full account.
16. A related Claisen rearrangement has been reported for the total synthesis of (±)-annonene, a trans-clerodane diterpene. See, Takahashi, S., Kusumi, T., Kakisawa, H., Chem. Lett., 1979, 515-518.
17. 2, etc.). See, Crabtree, R. H., Davis, M. W., J. Org. Chem., 1986, 51, 2655-2661.
18. Grieco, P. A., Gilman, S., Nishizawa, M., J. Org. Chem., 1976, 41, 1485-1486.
19. After purification by column chromatography on silica gel, this compound was immediately used for the next coupling reaction due to its instability.
20. Takai, K., Hotta, Y., Ohsima, K., Nozaki, H., Bull. Chem. Soc. Jpn., 1980, 53, 1698-1702.
21. Tokoroyama, T., Kanazawa, R., Yamamoto, S., Kamikawa, T., Suenaga, H., Miyabe, M., Bull. Chem. Soc. Jpn., 1990, 63, 1720-1728.
22. D+8.3° (c 0.18, CDCl3). This is probably due to its instability in a choroform-d solution.